Upper Matecumbe Key condominium resorts to rent

"We absolutely loved our stay at cheeca, will not be our last!"

"Great view! Sweet ppl that work there!"

"Absolutely heavenly! Comfy beds, clean and an fun perks like a local shuttle and water taxi! Cute activities and amazing sister resort privileges! Thank you so much! "

"Great place"

" We’ve been visiting Islander since 2015, and each stay continues to exceed our expectations. From the moment we arrive, the warm and welcoming staff make us feel like family in particular Angela and Sarah .Their attention to detail and genuine hospitality have kept us returning year after year. The rooms are consistently comfortable, clean, and beautifully maintained, with lovely views and thoughtful amenities that make our stay special. The hotel’s ambiance strikes the perfect balance between luxury and comfort, making it an ideal place to relax and unwind. We also love the dining options — the restaurant offers delicious local and international cuisine. Highly recommended for anyone seeking a reliable, welcoming, and top-quality hotel experience! "

"A must stay"

"I love this place, it’s chill, dog friendly, ramp and docks for ease of throwing in my paddleboard. Insanely beautiful views, and central to everything."

"The people were friendly, property was well cared for. The resort was really nice. We enjoyed it all."

"Absolutely wonderful. Will be back!!"